Compounds
ID | Spectrum Quality | Annotated Name |
---|---|---|
CCMSLIB00000478499 | Silver | Stephacidin&A_130074 |
CCMSLIB00000478500 | Silver | Stephacidin&A_130074 |
COMPOUND NPA010784
PROPERTIES
NPAID | NPA010784 |
---|---|
CLUSTER ID | 193 |
NODE ID | 181 |
NAME | Stephacidin A |
FORMULA | C26H29N3O3 |
MOLECULAR WEIGHT (Da) | 431.5360 |
ACCURATE MASS (Da) | 431.2209 |
ORIGIN ORGANISM TYPE | Fungus |
ORIGIN GENUS | Aspergillus |
ORIGIN SPECIES | ochraceus |
InChIKey | YCWBTRJVYADFLQ-IMDCKVJKSA-N |
InChI | InChI=1S/C26H29N3O3/c1-23(2)10-8-15-17(32-23)7-6-14-16-12-26-18(24(3,4)20(16)27-19(14)15)13-25(21(30)28-26)9-5-11-29(25)22(26)31/h6-8,10,18,27H,5,9,11-13H2,1-4H3,(H,28,30)/t18-,25+,26-/m0/s1 |
SMILES | CC1(C)C=CC2=C(C=CC3=C2NC2=C3C[C@@]34NC(=O)[C@@]5(CCCN5C3=O)C[C@H]4C2(C)C)O1 |
ORIGINAL ISOLATION REFERENCE
CITATION | Qian-Cutrone, Jingfang; Huang, Stella; Shu, Yue-Zhong; Vyas, Dolatrai; Fairchild, Craig; Menendez, Ana; Krampitz, Kimberly; Dalterio, Richard; Klohr, Steven E.; Gaot, Qi Stephacidin A and B: Two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells Journal of the American Chemical Society 2002 124 (49) 14556-14557. | ||
---|---|---|---|
DOI | 10.1021/ja028538n | PMID | 12465964 |
SYNTHESES
CITATION 1 | Greshock TJ; Grubbs AW; Jiao P; Wicklow DT; Gloer JB; Williams RM Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600. Angewandte Chemie International Edition 2008 47 (19) 3573-3577. DOI: 10.1002/anie.200800106 PMID: 18389509 | ||
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CITATION 2 | Baran PS; Guerrero CA; Ambhaikar NB; Hafensteiner BD Short, enantioselective total synthesis of stephacidin A. Angewandte Chemie International Edition 2005 44 (4) 606-609. DOI: 10.1002/anie.200461864 PMID: 15586393 | ||
CITATION 3 | Greshock TJ; Grubbs AW; Tsukamoto S; Williams RM A concise, biomimetic total synthesis of stephacidin A and notoamide B. Angewandte Chemie International Edition 2007 46 (13) 2262-2265. DOI: 10.1002/anie.200604378 PMID: 17304610 | ||
CITATION 4 | Sunderhaus JD; McAfoos TJ; Finefield JM; Kato H; Li S; Tsukamoto S; Sherman DH; Williams RM Synthesis and bioconversions of notoamide T: a biosynthetic precursor to stephacidin A and notoamide B. Organic Letters 2013 15 (1) 22-25. DOI: 10.1021/ol302901p PMID: 23249380 | ||
CITATION 5 | Greshock TJ; Williams RM Improved biomimetic total synthesis of D,L-stephacidin A. Organic Letters 2007 9 (21) 4255-4258. DOI: 10.1021/ol701845t PMID: 17854197 | ||
CITATION 6 | Artman GD; Grubbs AW; Williams RM Concise, asymmetric, stereocontrolled total synthesis of stephacidins A, B and notoamide B. Journal of the American Chemical Society 2007 129 (19) 6336-42. DOI: 10.1021/ja070259i PMID: 17455936 |
REVISIONS
VERSION | SMILES | CITATION | ||
---|---|---|---|---|
Original Isolation | CC1(C=CC2=C(O1)C=CC3=C2NC4=C3CC56C(C4(C)C)CC7(CCCN7C5=O)C(=O)N6)C | Qian-Cutrone, Jingfang; Huang, Stella; Shu, Yue-Zhong; Vyas, Dolatrai; Fairchild, Craig; Menendez, Ana; Krampitz, Kimberly; Dalterio, Richard; Klohr, Steven E.; Gaot, Qi Stephacidin A and B: Two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells Journal of the American Chemical Society 2002 124 (49) 14556-14557. DOI: 10.1021/ja028538n PMID: 12465964 | ||
2 | CC1(C)C=CC2=C(C=CC3=C2NC2=C3C[C@@]34NC(=O)[C@@]5(CCCN5C3=O)C[C@H]4C2(C)C)O1 | Baran, Phil S; Hafensteiner, Benjamin D; Ambhaikar, Narendra B; Guerrero, Carlos A; Gallagher, John D Enantioselective total synthesis of avrainvillamide and the stephacidins. Journal of the American Chemical Society 2006 128 (26) 8678-93. DOI: 10.1021/ja061660s PMID: 16802835 |